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Holiday Rentals with Pools in Simon's Town

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    AU$231 Average
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    Travellers to Simon's Town are booking October dates now. Secure your holiday rental today, and have the perfect trip.
    20 Matching Rentals in Simon's TownView all 87 rentals
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    Camilla1 / 32
    (38)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Modern Apartment at Boulders Penguin Colony1 / 70
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Rocklands House, Beach –Front Holiday Home1 / 16
    (13)Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Sauna
    • Waterfront
    • Mountain Views
    • Wi-Fi
    • Ocean Views
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 23 April 2018
    From the breath taking views of the ocean to the many creature comforts of the Rockland house my mom's 60th birthday weekend was a hit!We'll definitely be back!
    Reviewed 9 June 2017
    This is our second stay and was even better than the first time we stayed. Great facilities and wonderful view. Very attentive landlord but not intrusive. We really appreciated...
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    About this property
    Rocklands house, beach –front holiday home murdoch valley simon’s town. The perfect weekend getaway or holiday retreat to de-stress and unwind. So tranquil, it feels like you are sailing on your own ocean liner! Comfortably furnished, double-storey holiday home overlooking false bay just...
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    Location Information
    7975, Simon's Town, Cape Town
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    The View, Simonstown1 / 10
    (5)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Patio
    • DVD Player
    • Cable/satellite TV
    • Secure Parking
    • Private Outdoor Pool (Heated)
    • Grill
    • Balcony
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 January 2018
    We had a wonderful family holiday at The View in Simon'sTown. All of us were feeling wonderful and enjoyed the stunning view and the spacious house. The kids especially enjoyed...
    Reviewed 5 September 2017
    The View is close to Simon's Town which is the historic naval base near the Southern tip of the Cape Town peninsula, so it provides easy access to nearly 3 centuries of historic...
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    About this property
    Backing onto the mountain above Simonstown, The View boasts a stunning panorama of False Bay from two bedrooms as well as the dining room and lounges. The open plan living area opens out onto a patio which is the ideal spot to soak up the sun and the view of the sea. We have seen whales,...
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    Location Information
    7975, Simon's Town, Cape Town
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    PINGUSHOUSE  VILLA WITH PRIVATE POOL & GARDEN1 / 25
    (10)Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Wi-Fi
    • Washer
    • Parking
    • Balcony
    • Private Outdoor Pool (Heated)
    • Ocean Views
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 22 April 2016
    This house could have an amazing panoramic view of almost the whole of False Bay, but it is blocked by a fortress of extremely high hedges. It is so frustrating. That...
    Reviewed 15 December 2015
    We was 6 friends and was for one week in Pingushouse. The house is wonderful, with a great view to the sea.We had a great time at simon's town and we will come back.The...
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    About this property
    Situated in Simon's Town, near Boulders Beach were the penguins live, PingusHouse is a 4 bedroom holiday home with a nice private secluded garden and solar heated swimming pool. It is also within a five minute walk from incredible secret little beaches, with natural crystal clear water pools...
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    Location Information
    7975, Simon's Town, Cape Town
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Famous Designed Home With Pool & Amazing Views1 / 16
    (1)Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Patio
    • Cable/satellite TV
    • Balcony
    • Internet Access
    • Parking
    • Private Outdoor Pool (Unheated)
    • Washer
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Simonstown Self Catering Accommodation: This minimalistic luxury Simonstown self-catering accommodation has 4 en-suite bedrooms and is designed to accommodate 8 persons. The architectural design was for a holiday home & is intentionally minimalist with exposed concrete, lime-washed wood, galvanised...
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    Location Information
    7995, Simon's Town, Cape Town
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Amenities & Details
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Grill
    • Mountain Views
    • Patio
    • Secure Parking
    • Ocean Views
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    •Well Equipped Kitchenette with Granite Worktop, 2 plate stove, Microwave, Toaster, Kettle and Coffee Machine •Extra Large Double Room with Queen Bed, Single Bed and Built In Wardrobes, Dressing Table and Stool •Living room with Leather Couches and Flat Screen TV with Satellite TV, Hotel Package...
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    7975, Simon's Town, Cape Town
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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    2 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Amenities & Details
    • Private Garden
    • Patio
    • Secure Parking
    • Grill
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This 2 bedroom villa can be split into 2 apartments and boasts one of the most stunning sea views in Simon's Town. The front of the villa looks over the sea and has a separate BBQ/Sun room. The front of the villa has a living room, bedroom and BBQ/Sun room which faces directly onto the sea with...
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    Location Information
    7975, Simon's Town, Cape Town
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 7
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    6 Bedrooms, 6 Bathrooms, Sleeps 13 Quick View
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    Amenities & Details
    • DVD Player
    • Waterfront
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Cable/satellite TV
    • Ocean Views
    • Mountain Views
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    At Fisherman's Cove, you'll be staying in one of the houses for which the now famous Boulder's Beach at Simons Town was once a private paradise. Incredible views from your bed and breakfast table. Watch the penguins jumping off the rocks in serried ranks as they set out for the open sea, swim with...
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    Location Information
    7975, Simon's Town, Cape Town
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 13
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Wi-Fi
    • Terrace
    • Ocean Views
    • Balcony
    • Secure Parking
    • Private Outdoor Pool (Unheated)
    • Mountain Views
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    At Seascapes offers a secure and peaceful seaside location close to historic Simonstown on the False Bay coast. The house is well appointed, well equipped and offers spectacular views over False Bay. A five minute walk will take you to fishermans beach (featured on Getaway magazine) or a stroll up...
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    Location Information
    7975, Simon's Town, Cape Town
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Rocklands House1 / 23
    (4)Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Ocean Views
    • DVD Player
    • Mountain Views
    • Cable/satellite TV
    • Private Outdoor Pool (Unheated)
    • Hot Tub
    • Wi-Fi
    • Sauna
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 March 2017
    Such a fantastic holiday home that comfortably sleeps 8. The house is exactly what is shown in the photos. The view is stunning with ocean views upstairs and downstairs. We were...
    Reviewed 30 September 2015
    It's always difficult to be away from your own home and to go with friends you have never gone away can make for a tense breakaway. This was not the case at all. Generous space...
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    About this property
    ROCKLANDS HOUSE, BEACH –FRONT HOLIDAY HOME Murdoch Valley Simon's Town. The perfect weekend getaway or holiday retreat to de-stress and unwind. So tranquil, it feels like you are sailing on your own Ocean Liner! Comfortably furnished, double-storey holiday home overlooking False Bay just...
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    Location Information
    7976, Simon's Town, Cape Town
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Bahari Beach Villa1 / 17
    (1)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Private Garden
    • Wi-Fi
    • Parking
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 May 2017
    This huge, modern home has views that will blow you away. The nicest place we've ever stayed in Simonstown.
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    About this property
    The Bahari Villa boosts end to end sea views which are spectacular. The villa was recently renovated and extended and decorated to give a feel of openness, and relaxation. The open plan kitchen - dining - and living room area creates the most amazing views and ambience, and allows for a group or...
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    Location Information
    7975, Simon's Town, Cape Town
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Terrace
    • Private Garden
    • Balcony
    • Housekeeping Included
    • Patio
    • Secure Parking
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    'Phoenix Rising' is one of the highest houses on the mountainside above the Boulders Beach, famous for a large colony of African Penguins, with awe inspiring sea views across False Bay. From the Aloe and Protea garden behind the house you can climb straight up Swartkop mountain along the ridge to...
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    Location Information
    7975, Simon's Town, Cape Town
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Blue Mountain Bay Two1 / 12
    (2)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Private Garden
    • Cable/satellite TV
    • Wi-Fi
    • Secure Parking
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 July 2016
    We loved the view, the pool table, the barbeque facilities and the super-friendly hosts. Two three-quarter beds side-by-side were pure luxury, as were the crisp white cotton...
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    About this property
    Blue Mountain Bay is situated in the beautiful Murdock Valley in Simon's Town, on the route to Cape Point. The town is well known for its history and tradition as well as Boulders Beach with its world famous penguin colony. During the whale season, whales and dolphins can often be seen and...
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    Location Information
    7975, Simon's Town, Cape Town
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Simon's Town - 3 on Rocklands Beach and Pool Villa1 / 88
    (1)Very good
    3 Bedrooms, 4 Bathrooms, Sleeps 11 Quick View
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    Amenities & Details
    • Grill
    • Patio
    • Private Outdoor Pool (Unheated)
    • Mountain Views
    • Cable/satellite TV
    • Waterfront
    • Ocean Views
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This beautiful Beach Villa has recently opened and so far we are extremely lucky with fantastic reviews. The villa is split into 3 apartments which allows you to close interlocking doors if you need privacy, or open up the doors in order for a large group to entertain. Each apartment has a large...
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    Location Information
    7975, Simon's Town, Cape Town
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 11
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    La Pergola Garden Suite with pool, and stunning views1 / 21
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Grill
    • Cable/satellite TV
    • Patio
    • Ocean Views
    • Housekeeping Included
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 27 March 2018
    This exceptionally well equipped property – which is ideal for those seeking more than just the perfect base from which to explore the Cape Peninsular - is exactly as described...
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    About this property
    Located high on the mountainside above Simon's Town, La Pergola Garden Suite has breathtaking views over False Bay and the historic naval harbour. An easy walk takes you down to the quaint shops and restaurants in the town, and a few minutes drive to the penguins at Boulders Beach. The apartment...
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    Location Information
    7995, Simon's Town, Cape Town
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Blue Mountain Bay One1 / 10
    (1)Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Cable/satellite TV
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Blue Mountain Bay is situated in the beautiful Murdock Valley in Simon's Town, on the route to Cape Point. The town is well known for its history and tradition as well as Boulders Beach with its world famous penguin colony. During the whale season, whales and dolphins can often be seen and...
    View all property information
    Location Information
    7975, Simon's Town, Cape Town
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
    Make Enquiry
    4 Bedrooms, 4 Bathrooms, Sleeps 9 Quick View
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    Amenities & Details
    • Washer
    • Private Outdoor Pool (Unheated)
    • Balcony
    • Wi-Fi
    • Grill
    • Cable/satellite TV
    • Patio
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Boulders Beach Villa located at Boulders Beach, a sheltered beach made up of inlets between granite boulders where the name originates and home to a breeding colony of over 2000 endangered African Penguins. This two level coastal retreat is the perfect fully serviced luxury vacation rental for a...
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    Location Information
    7975, Simon's Town, Cape Town
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 9
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Private Garden
    • Internet Access
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located in Simonʼs Town, 16.1 km from Cape Point, Sunrise Sea Villa provides accommodations with free WiFi and a seasonal outdoor swimming pool. Some units have a terrace and/or a patio with sea or mountain views. The vacation home has a grill. If you would like to discover the area, hiking is...
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    Location Information
    7975, Simon's Town, Cape Town
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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